373-68-2Relevant articles and documents
Hydrogen bonding. Part 66. Further studies of the fluoride ion assisted dissolution of 1-methyl-4,5-dicarboxyimidazole: Absence of cation participation and stoichiometric considerations
Harmon, Kenneth M.,LaFave, Natalie J.
, p. 297 - 306 (1997)
Excess 1-methyl-4,5-dicarboxyimidazole (H2MDCI) dissolves into saturated solution in the presence of sodium fluoride, and precisely four F are required for each H2MDCI solubilized. To account for the apparent removal of two acidic hydrogens from H2MDCI in the presence of undissociated diacid we postulated strong complexation of Na+ by MDCI2-. We now find that the dissolution behavior of H2MDCI in the presence of either cesium or tetramethylammonium fluoride is identical to that with sodium fluoride. As cesium ion should bind weakly if at all to MDCI2-, and tetramethylammonium ion should not be bound, we conclude that the cation present plays no role in the fluoride ion assisted dissolution of H2MDCI. Analysis of dissolution stoichiometry and titration data suggests the possibility that two F- react with H2MDCI to form HMDCI+ and HF2/- and that two more F are required but do not act to abstract acid hydrogen.
Tetramethylammonium Fluoride Alcohol Adducts for SNAr Fluorination
Bland, Douglas C.,Lee, So Jeong,Morales-Colón, Mariá T.,Sanford, Melanie S.,Scott, Peter J. H.,See, Yi Yang
supporting information, p. 4493 - 4498 (2021/06/28)
Nucleophilic aromatic fluorination (SNAr) is among the most common methods for the formation of C(sp2)-F bonds. Despite many recent advances, a long-standing limitation of these transformations is the requirement for rigorously dry, aprotic conditions to maintain the nucleophilicity of fluoride and suppress the generation of side products. This report addresses this challenge by leveraging tetramethylammonium fluoride alcohol adducts (Me4NF·ROH) as fluoride sources for SNAr fluorination. Through systematic tuning of the alcohol substituent (R), tetramethylammonium fluoride tert-amyl alcohol (Me4NF·t-AmylOH) was identified as an inexpensive, practical, and bench-stable reagent for SNAr fluorination under mild and convenient conditions (80 °C in DMSO, without the requirement for drying of reagents or solvent). A substrate scope of more than 50 (hetero) aryl halides and nitroarene electrophiles is demonstrated.
A fluoride salt ion liquid synthetic method of the
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Paragraph 0244; 0245; 0246; 0247; 0248; 0249, (2016/10/10)
The invention relates to the field of organic chemical synthesis, particularly a synthesis method of a fluoride salt ionic liquid. The method comprises the following steps: adding excessive hydrofluoric acid, ammonium fluoride or ammonium bifluoride into halogenated imidazole and other raw materials, stirring in a closed environment, heating to 50-70 DEG C, and sufficiently reacting for at least 3 hours to obtain a non-dewatered fluoride salt ionic liquid; detecting, purifying and dewatering to obtain a thick liquid; and detecting the thick liquid to obtain the qualified fluoride salt ionic liquid. The method has the advantages of simple technique, no organic solvent, no waste and high end product purity.